In addition to sound technical skills, industry jobs require soft skills such as teamwork and good organizational abilities. This is even more important in today’s landscape, where working from the office is substituted with working from home. This trend, together with the shift towards distributed teams that are separated geographically and across time zones is expected to create challenges addressed through improved management and soft skills. Organizations of higher learning include the development of capstone or team projects as part of their curricula in order to prepare students for collaborative work and improve their organizational abilities. In this paper, we present an exploratory study focused on the challenges encountered by students in two consecutive iterations of a Team Projects course. The second iteration took place fully online due to the ongoing pandemic. We discovered the lack of face to face communication and schedule synchronization as some of the important challenges reported. We show that mitigating strategies by both teaching staff and the students themselves helped keep communication open and engagement high. We provide a replication package that allows repeating or extending our study.